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Why is it sad? If he is self-dealing between wordpress.org and Automattic, that's a big no-no. It sure looks from his comments here like he sees the two as one entity.

Also, the man outright said "use 'WP' since we think 'WP' is generic" and then cried "brand confusion" years later. If you want to avoid brand confusion, maybe don't tell people they can use your trademark?

You make it sound like it's a black eye against Kassabian.

In fact, many people believe that absolutely, if he has been lying to the IRS and self-dealing his way into a $400M net worth, then absolutely he deserves to lose the license to that trademark.

Why sad? If he defrauded the government, he’s got bigger problems than losing a trademark.

Matt doesn’t own the trademark, the Wordpress Foundation does. Losing a lawsuit to WP Engine would not change that.

I think it was explained elsewhere, but Automattic has the commercial trademark rights, partly because they owned the trademark before the WP foundation was created.